Oxirane, 2-propyl- → Phthalimide

HRID 1014668Notes

Reaction equation

HRID 1014668 reaction equation
OC1C=C(CCC[N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])C=CC=1.O1C(CCC)C1>>[C:12]1(=[O:21])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[NH:11]1

Participants

3

Reactant 2

HCID 13853Oxirane, 2-propyl-HCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 6809Phthalimide

Procedure

Alkylation reaction of phenol 58 with 1,2-epoxypentane gave 2434342-hydroxypentyloxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (0.93 g, 73%): 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J=6.0 Hz, 1H), 7.53-7.60 (m, 1H), 7.47-7.52 (m, 1H), 7.40 (d, J=7.6 Hz, 1H), 7.14-7.19 (m, 1H), 6.78-6.83 (m, 2H), 6.73 (d, J=8.2 Hz, 1H), 3.81 (d, J=4.8 Hz, 2H), 3.73-3.79 (m, 1H), 3.18-3.24 (m, 2H), 2.60 (t, J=7.6 Hz, 2H), 1.73-1.81 (m, 2H), 1.30-1.52 (m, 4H), 0.89 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-4fb1cd8e84154ae9b5033c9fbfd5272f
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

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